Intramolecular butenolide allene photocycloadditions and ensuing retro-ene reactions of some photoadducts

European Journal of Organic Chemistry

Volumn , Issue 17, 2011, Pages 3146-3155

  Lutteke, Ginger ^a   Kleinnijenhuis, Roel A ^a   Jacobs, Ivo ^a   Wrigstedt, Pauli J ^a   Correia, Ana C A ^a   Nieuwenhuizen, Rowan ^a   Buu Hue, B T ^a   Goubitz, Kees ^a   Peschar, René ^a   Van Maarseveen, Jan H ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Cycloaddition; Cyclobutane; Photochemistry; Retro ene reaction; Silver mediated allylation; Small ring systems; Solanoeclepin A

Indexed keywords

EID: 79957790660     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100245     Document Type: Article

References (25)

1. For recent reviews, see, for example
2. T. Bach, J. P. Hehn, Angew. Chem. Int. Ed. 2011, 50, 1000-1045.
3. N. Hoffmann, Chem. Rev. 2008, 108, 1052-1103.
4. J. Iriondo-Alberdi, M. F. Greaney, Eur. J. Org. Chem. 2007, 4801-4815.
5. B. T. B. Hue, J. Dijkink, S. Kuiper, K. K. Larson, F. S. Guziec Jr., K. Goubitz, J. Fraanje, H. Schenk, J. H. van Maarseveen, H. Hiemstra, Org. Biomol. Chem. 2003, 1, 4364-4366.
6. B. T. B. Hue, J. Dijkink, S. Kuiper, S. van Schaik, J. H. van Maarseveen, H. Hiemstra, Eur. J. Org. Chem. 2006, 127-137.
7. for a recent review on [2+2] cycloadditions of allenes, see:, B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783-816.
8. C. W. Jefford, A. W. Sledeski, J. Boukouvalas, Helv. Chim. Acta 1989, 72, 1362-1370.
9. C. W. Jefford, A. W. Sledeski, J.-C. Rossier, J. Boukouvalas, Tetrahedron Lett. 1990, 31, 5741-5744.
10. J. Pornet, B. Randrianoelina, L. Miginiac, J. Organomet. Chem. 1979, 174, 1-13.
11. G. Lutteke, R. AlHussainy, P. J. Wrigstedt, B. T. B. Hue, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, Eur. J. Org. Chem. 2008, 925-933.
12. G. Casiraghi, G. Rassu, P. Spanu, L. Pinna, J. Org. Chem. 1992, 57, 3760-3763.
13. M. N. Wrobel, P. Margaretha, Helv. Chim. Acta 2003, 86, 515-521.
14. J. Meinwald, J. K. Crandall, J. Am. Chem. Soc. 1966, 88, 1292-1301.
15. G. Mehta, S. R. Singh, V. Gagliardini, U. D. Priyakumar, G. N. Sastry, Tetrahedron Lett. 2001, 42, 8527-8530.
16. P. Conti, A. P. Kozikowski, Tetrahedron Lett. 2000, 41, 4053-4056.
17. N. Jullian, I. Brabet, J.-P. Pin, F. C. Acher, J. Med. Chem. 1999, 42, 1546-1555.
18. M. Abe, E. Torii, M. Nojima, J. Org. Chem. 2000, 65, 3426-3431.
19. J.-L. Ripoll, Y. Vallée, Synthesis 1993, 659-677.
20. J. M. Cassady, S. R. Byrn, I. K. Stamos, S. M. Evans, A. McKenzie, J. Med. Chem. 1978, 21, 815-819.
21. H. M. R. Hoffmann, J. Rabe, Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110.
22. R. R. A. Kitson, A. Millemaggi, R. J. K. Taylor, Angew. Chem. Int. Ed. 2009, 48, 9426-9451.
23. H. Schenk, R. A. J. Driessen, R. de Gelder, K. Goubitz, H.Nieboer, I. E. M. Brüggemann-Rotgans, P. Diepenhorst, Croat. Chem. Acta 1999, 72, 593-606.
24. W. K. Appel, T. J. Greenhough, J. R. Scheffer, J. Trotter, J. Am. Chem. Soc. 1979, 101, 213-215.
25. See, e. g.:, D. Bellus, B. Ernst, Angew. Chem. Int. Ed. Engl. 1988, 27, 797-827.